8 Flagler Dr, Rye, NY 10580
OFF MARKET

8 Flagler Dr
Rye, NY 10580

  • 6 Beds
  • 6.5 Baths
  • 9,153 sqft (on 1.62 acres)

$5,604,300

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $34,925/mo*
Refinance Your Home

$5,604,300

Trulia Estimate
as of May 22, 2026
Est. Refi. Payment $34,925/mo*
Refinance Your Home
6 Beds
6.5 Baths
9,153 sqft
(on 1.62 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Custom-built Georgian brick Colonial located in the sought-after Flagler Matthew Estate area, just minutes from Metro North, Rye Country Day School and downtown Rye. Set on 1.62 level acres, the property features breathtaking views of the pond, soothing waterfall, manicured English gardens and rolling lawns. The first level is perfect for formal entertaining with grand entry foyer, formal living and dining rooms and English conservatory as well as comfortable everyday living in the family room, Christopher Peacock kitchen, study and sunny sitting area. The expansive patio provides a great spot for intimate outdoor dining as well as large-scale gatherings. The second level includes a stunning master suite with spa bath, sitting room with fireplace and boasting a balcony overlooking the pond and lush landscaped grounds. Four additional bedrooms with ensuite baths and a cozy second floor den complete the second level. This impressive home is not to be missed!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 8 Flagler Dr

Interior Features

Interior Details
Basement
Heating & Cooling
Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2
Fireplace & Spa
Fireplace

Property Information

Year Built
Year Built: 1997
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: Brick
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 1.62 acres

Price History for 8 Flagler Dr

DatePriceEventSource
10/27/2017$4,400,000Sold
OneKey® MLS as distributed by MLS GRID #H4727787
10/19/2017$4,800,000PendingAgent Provided
07/06/2017$4,800,000Listed For SaleAgent Provided
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Property Tax and Assessment

Year2025
Tax
Assessment$50,700
Home facts updated by county records

Comparable Sales for 8 Flagler Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
73 Park Drive S, Rye, NY
0.38
Single-Family Home
$7,200,000
11/10/25
6
7
8,585
325 Highland Road, Rye, NY
0.24
Single-Family Home
$3,950,000
09/23/25
4
5
4,687
14 Lakeside Drive, Rye, NY
0.15
Single-Family Home
$2,400,000
04/07/26
5
8
6,629
472 Purchase Street, Rye, NY
0.24
Single-Family Home
$2,856,651
07/17/25
6
4.5
5,243
1 Polly Pk Road, RYE, NY
0.34
Single-Family Home
$2,100,000
09/26/25
5
5.5
5,789
53 Park Drive S, Rye, NY
0.65
Single-Family Home
$6,700,000
05/22/25
6
7.5
9,248
5 Sunset Ln, Rye, NY
0.79
Single-Family Home
$8,000,000
08/25/25
7
6
8,352
15 Hillside Rd, Rye, NY
0.36
Single-Family Home
$1,100,000
07/08/25
6
5
4,593
26 GRISWOLD Road, Rye, NY
0.52
Single-Family Home
$4,300,000
09/10/25
5
5
6,545
19 Hilltop Place, Rye, NY
0.42
Single-Family Home
$10,750,000
10/03/25
9
10.5
11,236

Nearby homes

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Assigned Schools

These are the assigned schools for 8 Flagler Dr.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Rye

At least 150 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 84 % Say there's holiday spirit

  • 81 % Say kids play outside

  • 81 % Say yards are well-kept

  • 80 % Say people would walk alone at night

  • 77 % Say car is needed

  • 77 % Say parking is easy

  • 72 % Say it's quiet

  • 71 % Say streets are well-lit

  • 69 % Say it's walkable to restaurants

  • 66 % Say there's wildlife

  • 64 % Say they plan to stay for at least 5 years

  • 62 % Say there are sidewalks

  • 57 % Say neighbors are friendly

  • 56 % Say there are community events

  • 44 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Zjstempel
    "There are a lot of good public parks and nice sidewalks to walk on. also a lot of people own their own dogs"
    0
    Flag
  • Dbenzanava
    "Dogs owners would like it very much. There are special Dog bakeries & pet shops catering to your pet. "
    0
    Flag
  • Brianrollins1959
    "When we walk our dog.There is always someone else walking their dog.Every one usually picks up after their dog "
    0
    Flag
  • Brianrollins1959
    "I get on 287 in the AM . It’s a 15 minute ride to White Plains. But when l come home at 12:30pm . Every body is stressed out. And driving on my bumper. I have to watch because they almost running into me "
    3
    Flag
  • Felix Vazquez Jr
    "They send helpful information in the mailbox which allows us to find events that are happening in the town"
    2
    Flag
  • Trulia User
    "Very kid friendly - just note it’s not the Rye school system. Nice walking area around the Neightborhood"
    1
    Flag
  • Patricia I.
    "Halloween window displays on Puchase street by the school children. Christmas street fair on Purchase st."
    1
    Flag
  • Nickalvarez4
    "7 minutes to metro north. Good parking at train station. Trains on schedule. 37 min train ride in to Grand Central."
    0
    Flag
  • Ltifdle
    "Right now my commute is down the staircase. Otherwise very convenient to all highways (i287, hutch, i95) and trains to city."
    0
    Flag
  • Ltifdle
    "Homes have large yards where it’s safe for children to play. Stores and restaurants are conveniently nearby. Easy access to major roadways and trains to city."
    0
    Flag
  • Cleary.aileen
    "I live here and it’s really a great place to live , lots of great things go on here and great community spirit "
    1
    Flag
  • Rosemary
    "Green community lots of parks great schools. Nice main avenue luxury shopping. Bistro restaurants. Some Catholic Church around. "
    0
    Flag
  • Heatherosemusic
    "Grew up here with my grandma and I love it. It’s the quintessential suburbs with proximity to Manhattan, a quaint village, great schools, a beach, an amusement park and so much more. The ideal neighborhood to raise a family. "
    6
    Flag
  • Manonbartels2008
    "Short and easy, fast commute. Plenty of trains, on time and easy access. Parking at station is hard due to permit wait list."
    1
    Flag
  • Fernando
    "I love Rye. It is a very quiet and peaceful neighborhood. the place is nice with good restaurants. "
    1
    Flag
  • Trulia User
    "Rye has Metro North station with direct access to city. Also there are 2 major highways with 4 exits in Rye."
    1
    Flag
  • Dan K.
    "Extremely safe and well kept place to live and be! Definitely a higher price point than even other parts of Westchester, but it is what it promotes itself to be. "
    1
    Flag
  • Ltifdle
    "Wonderful neighborhood to raise a family. Can walk to the club for all types of sports year-round. Many choices for great schools. Close to town, doctors, worship."
    0
    Flag
  • Michael C.
    "Extremely beautiful every season. Very quiet, family friendly to a fault. Winding roads assure privacy and security. "
    3
    Flag
  • Lriddle
    "My neighborhood is convenient to Westchester county, greenwich / Stamford by car and or nyc by train."
    0
    Flag
  • John J.
    "It’s a pretty dog friendly neighborhood. Town park with great dog community few blocks away. Few places in town have water bowls out front. I’m guessing every 3rd house has dog. "
    2
    Flag
  • Lriddle
    "Storybook Main Street with shops and restaurants. Very convenient commuting to work opportunities in Westchester, Connecticut and nyc."
    0
    Flag
  • Cchidiya
    "everything is convenient and easily accessible even by foot. it's a beautiful neighborhood. people are friendly, restaurants are organic, shopping is amazing. there is always free parking everywhere."
    0
    Flag
  • Contessa1313
    "Best of all possible areas for schools, trains, buses, walking, bicyling, water sports, gardening,etc."
    0
    Flag

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8 Flagler Dr, Rye, NY 10580 is a 6 bedroom, 7 bathroom, 9,153 sqft single-family home built in 1997. This property is not currently available for sale. 8 Flagler Dr was last sold on Oct 27, 2017 for $4,400,000. The current Trulia Estimate for 8 Flagler Dr is $5,604,300.